Welcome to stick season in Vermont. This period of late fall — when the trees are mostly bare, the frenzy of foliage tourism has subsided and the snow hasn’t started to pile up — can be a great time to explore the state. We suggest spending some time in southern Vermont, and have highlighted several cozy, spooky, outdoorsy and historical activities to get your itinerary started.
Journalists from the New England News Collaborative have been on the road, seeking out the best local spots in the region. Find ideas here for other New England states. What to do if you’re a…
Book nerd
Southern Vermont is full of literary history, thanks in no small part to students and faculty of Bennington College. This region of the state has been pivotal in the lives of Robert Frost, Bret Easton Ellis, Jonathan Lethem, Donna Tartt, Lucy Terry Prince, John Irving, Rudyard Kipling and Shirley Jackson, among others.
Follow the Brattleboro Words Trail
In North Bennington, explore the world of Shirley Jackson
Jackson is known for the unsettling short story
The Lottery and the gothic horror novel
The Haunting of Hill House . The village celebrates Shirley Jackson Day with readings and festivities each June, if you happen to be visiting then, but fall is also an apt time to marinate in Jackson’s work. Jackson lived at 12 Prospect St. and 66 Main St. The homes are not open to the public, but you can view them while conducting your own
Jackson-themed walking tour . The Bennington Museum has several cat figurines that were owned by Jackson. Stop by the McCullough Free Library to find another of Jackson’s cat statues among the shelves — and what better place to sit down with some of Jackson’s literary works or her biography?
Visit Robert Frost’s house in Shaftsbury
Frost wrote
Stopping by Woods on a Snowy Evening at the house in June 1922, and he was also living there when he received his first Pulitzer Prize in 1924. The house is now a museum owned by Bennington College and is open select days from spring to early fall. From November to April, you’ll have to make an appointment and perhaps pay an additional fee;
see the museum website for more. After exploring the house, drive about 10 minutes south to the
Bennington Centre Cemetery to pay respects (and perhaps read some poetry) at Frost’s gravesite.
Go book shopping
All four of these bookstores are on the
Vermont Independent Bookstores Passport , so you can start gathering stamps. If you visit at least five bookstores, you can win prizes — but the real prize is recognizing the value of these bookstores in Vermont’s communities.
Admire the unsung artistry of stone walls
Walk around
Stone Wall Park at Scott Farm in Dummerston any time during daylight hours. This is where experts in dry stone walls have shown off their mastery. You can also stop by Scott Farm Orchard for heirloom apples and other fruit. Rudyard Kipling’s home (see above) is right next door.
Check out the contemporary art exhibits at the Brattleboro Museum and Art Center
Pro tip: The museum has several fun traditions including a Domino Toppling Extravaganza every fall (in 2024, it was on Oct. 6) and a recurring “Glasstastic” exhibit that has glass artists make real sculptures based on kids’ drawings of imaginary creatures.
Steep yourself in even more visual art
Bennington Museum boasts the largest public exhibition of Grandma Moses’ paintings in the world, along with other exhibits of art, pottery and local history. About 40 minutes north is the Southern Vermont Arts Center in Manchester, with another impressive suite of exhibits.
Explore a restored Pullman railcar and learn about the Black porters
Abraham Lincoln’s son, Robert Todd Lincoln, built an estate in Manchester that’s now known as Hildene, the Lincoln Family Home. You can tour the mansion, formal gardens, farm and trails. Don’t miss the restored Pullman railcar (Robert Todd Lincoln was president of the Pullman company) and explore the exhibit about the Black porters who worked for the Pullman Company. Hildene is a stop on the
Vermont African American Heritage Trail .
Learn about the Battle of Bennington
This pivotal Revolutionary War battle prevented British troops from capturing the Bennington supply depot. The fighting took place across state lines, in New York. The former site of the depot is now marked by a tall monument where you can learn the history.
Take a walking tour of one of Vermont’s oldest towns
Buildings in Bennington date as far back as the 1760s, and the town has shared a
self-guided walking tour of 27 historic highlights. Architectural and Revolutionary War history buffs, rejoice.
Take a scenic drive
Try the Molly Stark Byway, which is Route 9 from Bennington to Brattleboro, for some beautiful views. Stop at the Hogback Mountain Country Store in Marlboro for the famous “100 mile view” overlook.
Cast a line into the history of angling
Fly fishing enthusiasts will enjoy the
American Museum of Fly Fishing in Manchester, right next to the Orvis flagship store.
Take a walk
There are many options for easy hikes in the region; one is the
Hoot, Toot and Whistle Trail in Wilmington, which runs along a former railroad bed and ends at Harriman Reservoir. (If it's warm, you can take a dip.)
Hike, ski, bike or get a ride to the summit of Mount Snow
This ski resort has plenty to offer even when it’s not covered in snow. Several trails take you to the top, where you’ll get a view of Somerset Reservoir. In warmer months you can take the Bluebird Express lift up and down the mountain (or just down the mountain, after you’ve hiked to the summit).